| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1361930 | Bioorganic & Medicinal Chemistry Letters | 2011 | 4 Pages |
Solamargine, (25R)-3β-{O-α-l-rhamnopyranosyl-(1→2)-[O-α-l-rhamnopyranosyl-(1→4)]-β-d-glucopyranosyloxy}-22α-N-spirosol-5-ene, has been synthesized in 13 steps in a 10.5% overall yield starting from the naturally abundant diosgenin. Condensation of a partially protected glucopyranosyl donor with an oxaza-spiro moiety, which was formed in one-pot azido reduction, significantly improved the synthesis of desired molecule. The target compound exhibited good cytotoxic activities against tumor cells HeLa, A549, MCF-7, K562, HCT116, U87, and HepG2 with IC50 ranging from 2.1 to 8.0 μM.
Graphical abstractSolamargine has been synthesized in 13 steps and 10.5% overall yield from the natural abundant diosgenin.Figure optionsDownload full-size imageDownload as PowerPoint slide
